Some people love Role Playing more than others. And then there are the people who go above and beyond, role playing as two or more people at the same time.

Tell your story about the times when a player was acting two roles at the table, two different characters. Bonus points for stories where the player was successfully arguing with / against himself as the characters.

I've been playing in a 5th Edition D&D game which only has one other person involved (they're also the DM). I'm using a shy Raccoonfolk (homebrew race) Illsionist Wizard and a kleptomaniac human Rogue who got into thievery to avoid an arranged marriage. The DM's using a Tiefling Healing Domain Cleric and Half-Orc Barbarian. I'll admit I tend to struggle to RP 2 separate characters at once but I don't think it's going too badly on that front.

I was DMing another game where I ended up playing as 2 DMPCs because the player liked an enthusiastic anthro fox NPC Wizard who was only meant to be in 2 scenes. RPing her and the introverted Beastfolk (another homebrew race which are basically humans with fur and some animal features like tails and horns) Rogue at the same time didn't go as well due to the need for me to do other things rather than just focussing on roleplaying as my characters.

Not quite. The character in question really wouldn't want to have blood on him like that, which is ironic considering his preference for save-or-lose/die spells and debuffs like Sensory Depravation and Enevation.

Trust me, that character isn't overfond of blood either, but he's an incredibly weak mage by his race's standards and the setting's dragons are immune to direct magic anyway.
Besides which, there's no blood in that image.

By the time I read it he'd moved that to a separate archive, and now the archives have been stripped down - no archive menu to select a page, just buttons for 'first,' 'previous,' 'next,' and 'current.' The URLs for pages change around the time the dragon encounter is resolved, too, so navigating past 600ish by URL doesn't work.

But... I already told this story resently. I'm not repeating it again. Wait, I actually forgot, that I technically played 3 characters that time. Even 4, but the 4th one was a one-shot to pass some time when my other characters were unavailable for story reason.
Confused yet? It's not that complicated. There was 2 characters that I made sure never met because they would be at each other's throat in no time. But one of them was actually two characters in one body: the first possessed the second, taking control. Kinda like in Superior Spiderman, only the second one was less "good infuence" and more "stupid distraction." And instead of hating each others guts they bonded with each other over their situation. I was planning for them to eventially separate to different bodies and continue to live as buddy-buddy to each others, but because the campain was so bad, I grown to hate it and just abaddoned all my ideas.

I think it has only happened twice and neither time was how the campaign originally was intended.

One was a GURPS setting; I think no magic (it might have been there but secret and subtle) but otherwise a fairly typical pseudo-medieval fantasy feel (just strip out blatantly magical bits). Yeah, I've brought this one up before: the PCs were all mercenaries that were part of the same unit.

The short version is that we realized we needed more people to take things where both GM and players wanted it to go, but the session where we'd invited several extra people (I'd even invited three different people and built characters for them)... none showed up. Maybe it was just me, maybe it was some of the others as well, but I was allowed to run both my normal archer (Hans) and a front line fighter intended to be a bit of a "thug" I named Lister.

I found ways in game to help the two become friends, and since then when I've tried to recreate them elsewhere, I've simply made the two family (with the appropriate rewards and obligations) to justify them looking out for each other. Hans tends to handle rural or actual wilderness survival while Lister focuses on urban and dealing with less savory types. Both can do ranged or melee combat but Hans is of course better at the former and Lister at the latter. Not overly exciting, but clearly I enjoyed it. XD

A bit more interesting is the second time it happened; Star Wars RPG (I forget the proper term but it was a d6 based one). I was running a Gamorrean that had been able to overcome their innate hostility to droids: a huge "cheat" but the GM agreed to it (memory is really hazy - might have been "Oh crap we both forgot about this until we basically needed to hand wave it for both player and GM convenience" moments).

The Gamorrean (...he had an annoying habit of changing his name because I couldn't come up with a good one =P) thus had an astromech droid because he frankly needed one for the fighters he was often piloting. One thing led to another and eventually he got upgraded more and more and finally the GM just had me run him as a secondary character. Probably because by that time both he and I were jonesing for a Transformers RPG (...yes, eventually my former astromech droid got an alternate mode).

...

I'm telling you this only sounded halve as stupid (or twice as stupid awesome!) if you were there! XD

In a campaign where we were short on players, practically everyone was playing at least two people. I myself played a pyromaniac wizard and a paladin. The wizard often introduced the paladin as his parole officer.
Come to think of it, I never did decide if he was serious.

So in my Ponyfinder campaign, everyone is married. And because we're all ponies, this means polygamy, or herds. Overwatch is my main PC. Then there's Dappled Spirit, the Lead Mare and professional worrywart; Cool Evening, the Celebrity Bard and carefree soul with a fear of responsibility, and Lily the Necrodruid, who is the most motherly, kindest, and most likely to turn you into an undead helper of you hurt her children.

There's also three children in the Overherd. Aurora Role, an adopted seapony filly who was a Demon Lord about five minutes before we adopted her, Oversoul, a pegasus filly who rolled a Nat 20 on her Beauty Score at birth (just like her father!), and Depth Perception, who is already planned to be my next PC.

Usually, we do RPs through text over Skype, but there was one time where I RP'd the entire Herd arguing and trying to get ready to go somewhere when the other PCs showed up to get Overwatch for a new mission. The GM was flabbergasted that is been able to keep track of an impromptu argument like that, even if it was a short one.

Once introduced an evil-aligned misanthropic druid who was supposed to stick with the party out of sense and practicality instead of friendship. Then our first encounter was against wild animals, and when he calmed them down, the party kept attacking them. So... yeah. He left in a huff. I brought in a new character, solidly good-aligned. Meanwhile, the druid gained control of a town. And then the two met, leaving me running both a PC and the villain of the arc.

That's fairly common with PC's Evil characters are cautious out of self interest and play it low assuming everybody will think it's ok to attack them while Good PC's assume since they're "Good" that they can do whatever they feel like and be in the right.

I played a highly insane villain and her much saner sidekick. Villain was my fusion of Harley Quinn and Quackerjack from Darkwing Duck. Her sidekick was an ai robot rabbit who had to obey her orders but tended to treat the villainess as a kid sister, humoring her. It must have worked well because the heroes kept trying to recruit the rabbit.

During the Bleach of the Gods game we each had many opportunities to play side characters. Whether it was just fleshing out parts of the world, doing side stories etc. So every so often someone would end up talking to themselves if a side character returned.

Unless you were one particular member.

See, she had to leave the game for a few months due to being in New Zealand, during which time her character was kidnapped. On her return, we hadn't rescued her character yet, so she made a comic relief ninja to play until then. Then we rescued her character, but ninja kept turning up. So often in fact that aside from her doing voices, we also had her wear a hat to distinguish when she was being the ninja.

THEN it turned out that the one we rescued was actually an enemy shape-shifter. Even after actually rescuing her character for real she continued to also play the shape-shifter and the ninja, her actual character AND any other side characters she had made.

Fortunately, we had many hats available, which paid off when she had to be 3 different characters at once.

During an official campaign we were part of a ship's crew. The campaign book mentioned a few NPCs who only there to cover any strength the party might be lacking. It just so happened there were as many NPCs as PCs so everyone got an expy. Mine was an hommage to Queequeg only he was chewing considerable amount of 'happy weeds' and had deep conversations with his sabre.

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